3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Base Information

• Chemical Name: 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• CAS No.: 173097-81-9
• Molecular Formula: C₄₁H₆₅N₇O₈Si
• Molecular Weight: 812.095

Synonyms:3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Chemical Property of 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Chemical Property:

Purity/Quality:

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Technology Process of 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

There total 6 articles about 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (21950-36-7) → 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (173097-81-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Et₃N / acetonitrile / 3 h / Ambient temperature

2: 77 percent / CH₂Cl₂ / 18 h / Ambient temperature

3: 82 percent / 80 percent formic acid / H₂O / 8 h / Ambient temperature

4: 36 percent / 1H-imidazole / pyridine / 18 h / Ambient temperature

With 1H-imidazole; formic acid; triethylamine; In pyridine; dichloromethane; water; acetonitrile;

DOI:10.1002/hlca.19950780711

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (173097-81-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NaHCO₃ / H₂O; pyridine / 18 h / Ambient temperature

2: NaN₃ / dimethylformamide / 0.67 h / 65 - 68 °C

3: conc. NH₄OH, PPh₃ / pyridine / 18 h / Ambient temperature

4: 95 percent / Et₃N / acetonitrile / 3 h / Ambient temperature

5: 77 percent / CH₂Cl₂ / 18 h / Ambient temperature

6: 82 percent / 80 percent formic acid / H₂O / 8 h / Ambient temperature

7: 36 percent / 1H-imidazole / pyridine / 18 h / Ambient temperature

With 1H-imidazole; ammonium hydroxide; formic acid; sodium azide; sodium hydrogencarbonate; triethylamine; triphenylphosphine; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.19950780711

Reference yield:

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine (34245-48-2) → 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (173097-81-9)

Guidance literature:

Multi-step reaction with 5 steps

1: conc. NH₄OH, PPh₃ / pyridine / 18 h / Ambient temperature

2: 95 percent / Et₃N / acetonitrile / 3 h / Ambient temperature

3: 77 percent / CH₂Cl₂ / 18 h / Ambient temperature

4: 82 percent / 80 percent formic acid / H₂O / 8 h / Ambient temperature

5: 36 percent / 1H-imidazole / pyridine / 18 h / Ambient temperature

With 1H-imidazole; ammonium hydroxide; formic acid; triethylamine; triphenylphosphine; In pyridine; dichloromethane; water; acetonitrile;

DOI:10.1002/hlca.19950780711

upstream raw materials:

2',3'-isopropylidene adenosine

5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-O-<2-cyanoethyl N,N-diisopropylphosphoramidite>

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